(S)-diethyl 4-(bis(2-phenylallyl)amino)-(Z)-hept-2-enedioate | 1428150-19-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-diethyl 4-(bis(2-phenylallyl)amino)-(Z)-hept-2-enedioate
• 英文别名: diethyl (Z,4S)-4-[bis(2-phenylprop-2-enyl)amino]hept-2-enedioate
• CAS: 1428150-19-9
• 化学式: C₂₉H₃₅NO₄
• 分子量: 461.601
• InChiKey: APZGFRHXNCFQDA-MFUHEYGDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  34
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  diethyl 4-[bis(2-phenylprop-2-enyl)amino]hept-2-ynedioate 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 1,1,3,3-四甲基二硅氧烷 、 溶剂黄146 、 三(邻甲基苯基)磷 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以84%的产率得到(S)-diethyl 4-(bis(2-phenylallyl)amino)-(Z)-hept-2-enedioate
  参考文献：
  名称：

  Two Approaches toward the Formal Total Synthesis of Oseltamivir Phosphate (Tamiflu): Catalytic Enantioselective Three-Component Reaction Strategy and l-Glutamic Acid Strategy

  摘要：

  Two independent formal total syntheses of oseltamivir phosphate were successfully achieved: the first utilized a copper-catalyzed asymmetric three-component reaction strategy, and the second utilized L-glutamic acid gamma-ester as a chiral source to install the correct stereochemistry. Both strategies used Dieckmann condensation to construct a six-membered ring core, after which manipulation of the functional groups and protecting groups accessed Corey's intermediate for the synthesis of oseltamivir phosphate. While the first synthesis was accomplished via four purification steps in 25.7% overall yield, albeit with moderate optical purity (76% ee), the second strategy achieved the synthesis via six purification steps in 19.8% overall yield with perfect enantiocontrol.

  DOI：

  10.1021/jo400360j